Having visited almost every island in the Caribbean, I’m often asked which one stands out the most.
While we all picture swaying palms and sparkling turquoise waters, these 30 islands and territories offer so much more than the classic postcard scenes.
From coral cays to rainforest-covered mountains, and a mix of French, Spanish, Dutch, Irish, and Creole culture, there’s a flavour for every traveller.
To help you decide where to plant your sun-soaked feet this winter, here’s my guide to ten of my favourite islands and what makes each one special.
Best for Families: Antigua
If you’re looking for sun, sand, and family-friendly hotels, Antigua is a perfect pick.
Flights are just over eight hours, making it more accessible than some Caribbean destinations, and you can be sipping a welcome rum by the pool almost immediately.
The island boasts plenty of all-inclusive resorts, like the well-regarded Blue Waters Resort, which features a complimentary kids’ club complete with baby tortoises.
Other family-friendly activities include tie-dye workshops, fishing trips, and even croquet madness.
My Tip: Don’t miss English Harbour, home to the World Heritage-listed Nelson’s Dockyard and scenic coastal trails.
Book It: Seven nights at Blue Waters Resort from £5,096 per adult and £1,594 per child, all-inclusive, including British Airways flights from Gatwick on February 15 and transfers.
Beaches: Anguilla
For pure beach bliss, Anguilla delivers. This British Overseas Territory offers 33 pristine beaches, perfect for sunbathing or snorkelling, without the distraction of large tourist attractions.
Luxury resorts such as the clifftop Malliouhana and Aurora Anguilla Resort, which has a water park and golf course, provide first-class accommodation.
My Tip: Sail to Prickly Pear Cays for a lobster lunch aboard the 45-year-old hand-crafted boat, Tradition.
Book It: Seven nights at Zemi Beach House from £3,499 per person, room-only, including flights and transfers.
For Food Lovers: Grenada
Grenada, known as the Spice Island, offers more than just beaches.
Explore its mountainous interiors to see nutmeg, cacao, and tropical fruit cultivation.
The island is ideal if you prefer independent dining over all-inclusive options, with plenty of restaurants near Grand Anse Beach.
My Tip: Visit the historic River Antoine rum distillery, which has been producing rum with a water-powered wheel since 1785.
Book It: Seven nights at Coyaba Beach Resort from £1,720 per person, B&B, including flights and transfers.
Nature Lovers’ Paradise: St Lucia
St Lucia is a picture-perfect island famous for its iconic Pitons.
Climb Gros Piton for a rewarding four-hour hike, or enjoy the views from the sea.
The island is dotted with small luxury resorts such as Hotel Chocolat’s Rabot Estate and Anse Chastanet, which borders a marine reserve.
My Tip: Explore the island’s reptiles, butterflies, and flora through guided nature tours.
Book It: Seven nights at Anse Chastanet from £2,819 per person, room-only, including flights and transfers.
History Buffs: Barbados
This year marks 400 years since the arrival of the first English ship in Barbados, making it ideal for history lovers.
Explore St Nicholas Abbey, Codrington College, and the World Heritage-listed Garrison area in Bridgetown.
My Tip: Time your visit to catch the horse races at the historic Garrison Savannah track.
Book It: Seven nights at Coral Reef Club from £4,545 per person, B&B, including flights and transfers.
Hiking Heaven: Dominica
Dominica is the island for rainforest lovers. Tackle the 115-mile Waitukubuli National Trail or hike to Middleham Falls.
It’s less about beaches and nightlife, more about exploring lush landscapes.
My Tip: Soon, an Austrian-built cable car will take visitors to 2,600ft for a view of the Boiling Lake.
Book It: Seven nights at Jungle Bay from £2,640 per person, B&B, including flights, transfers, and car hire.
Romantic Getaway: British Virgin Islands
Perfect for couples, the British Virgin Islands offer serene beaches and luxurious resorts.
Rosewood Little Dix Bay on Virgin Gorda combines mid-century interiors with a stunning crescent of sand, complete with daily snorkelling and trips to nearby castaway beaches.
My Tip: Book a shared catamaran cruise to explore multiple islands with a skipper and chef.
Book It: Seven nights at Rosewood Little Dix Bay from £6,100 per person, B&B, including flights and transfers.
For Music Fans: Jamaica
Jamaica’s vibrant culture is perfect for music lovers and history buffs alike.
Visit the Bob Marley Museum, Tuff Gong recording studio, and the rural village of Nine Mile.
My Tip: Stay in multiple locations, including the Blue Mountains, to truly explore the island.
Book It: Nine-night tour from £2,089 per person, including accommodation, transport, activities, and breakfast; flights extra.
Old-School Charm: Nevis
Accessible via St Kitts, Nevis offers a quieter, old-school Caribbean experience with family-run hotels and a welcoming local vibe.
My Tip: Don’t miss the Friday night roadside barbecue outside Charlestown for jerk ribs and local culture.
Book It: Four nights at Montpelier Nevis plus three at Golden Rock Inn from £1,799 per person, B&B, including flights and transfers.
Pure Escape: Cayman Islands
Beyond the bustling Grand Cayman, Little Cayman offers tranquillity with just 170 residents and a large red-footed booby colony.
The island is perfect for diving at Bloody Bay Wall or enjoying quiet beaches.
My Tip: Cayman Brac is nearby for hiking, climbing, and stargazing adventures.
Book It: One night at Sunset House, Grand Cayman, plus six at Southern Cross Club, Little Cayman, from £7,200 per person, full board, including flights and transfers.